The Second Time Around

"The Second Time Around" is a song with words by Sammy Cahn and music by Jimmy Van Heusen. It was introduced in the 1960 film High Time, sung by Bing Crosby with Henry Mancini conducting his orchestra, and was nominated for the Academy Award for Best Original Song. It lost out to "Never on Sunday". Its theme is captured by its first two lines: Love is lovelier the second time around, Just as wonderful with both feet on the ground. Although Crosby recorded it on August 25, 1960, for MGM Records, it is especially associated with Frank Sinatra, who recorded it for Reprise Records on December 21, 1960. This achieved some chart success reaching the #50 position in the Billboard Hot 100 chart. Sinatra also recorded it again for Reprise on November 5, 1961, and April 29, 1963. Jane Morgan sang the song on a 1961 episode of The Jack Benny Program. Dame Kiri Te Kanawa performed this with André Previn on "The Jazz Album" (1992)